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4 Considerations Before Having that Difficult Conversation

“Be brave enough to start a conversation that matters” - Margaret Wheatley

It’s the 1980’s I’m a young manager running a successful retail business, and everything is going well when I realize I’m going to have “that difficult conversation” with an employee.

The employee is friendly mild-mannered and soft-spoken, but she’s not working out, and I put off having this conversation long enough – I’m not liking this side of leading very much.

It’s inevitable, sooner or later leaders are going to have that difficult conversation. Whether that conversation is correcting an employee’s costly mistake, letting someone go, or informing a good team member they’ve been passed over for that promotion; leaders understand that it comes with their job description.

I made the conversation simple to the point and as painless as I knew how to make it. Our talk was over, and I’m not sure who felt worse. I made it a point of assembling and managing the staff relationally which made this first difficult conversation all the more unpleasant.

It’s detrimental to an organization if a leader keeps putting off having difficult conversations especially if everyone on the team knows it needs to be done. I’m a relational leader and work at having team members get along; sometimes I must have those difficult conversations so the rest of the team can keep moving along.

If you’re a leader for some time, then you relate to that feeling in the pit of your stomach a day or two before having that “difficult conversation.” These conversations are never easy, and no one enjoys having them, but we can learn how to minimize the pain that often comes with the experience.

Having had some difficult conversations over the years has taught me a few things that may be of help to you as a leader when you find yourself having to have one.

4 Considerations Before Having That Difficult Conversation

“All people are deserving of respect, and we owe it to them to be truthful” - JSP

Consideration #1 - Don’t Put it Off

As tempting as it is to avoid it, the issue isn’t going to resolve itself. The longer you wait, the worse it gets. The following points can help you prepare:

  • Why must you have the conversation?

  • If you’re putting it off, ask yourself why?

  • How is this issue affecting your team?

  • Manage your emotion and collect your thoughts

  • Schedule the conversation

Consideration #2 - Check Your Ego at the Door

Having tough conversations require having the right motive and attitude.

  • How do you feel about the employee?

  • Is your motive personal or for the company as a whole?

  • Be clear in your thinking to communicate effectively

  • Empathy allows you to connect on a personal level

  • Your tone of voice, facial expressions, and body language speak louder than words

Consideration #3 - Listen More Speak Less

Reliable information is key to productive conversations, be sure you’re entering the meeting with facts and not hearsay.

  • Ask simple yet direct questions to separate fact from fiction

  • Allow the other person to ask questions, give honest answers

  • Listening protects the person, yourself, and your company

  • Be open-minded and affirm valid concerns they may have

  • Be open to the possibility of more than one perspective

Consideration #4 - Stay on Point

Difficult conversations can easily become complicated if you allow too much conversation to delay your getting to the issue at hand. It’s respectful to get to the point as quickly as possible; the person knows the purpose of the meeting.

  • Get to the point rather than talking around the issue.

  • Be direct sincere and cordial.

  • Choose your words carefully.

  • Map out the conversation and think over your questions.

  • Be prepared to answer questions.

“We have a deep desire to feel heard, and to know that others care enough to listen.” - Douglas Stone

*** This article was authored by John Picarello, Chief Leadership Officer at Lions Pride Leadership Co.***


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